During the Passover meal 4 cups of wine mixed with water are consumed. The name of the cups correspondent to the 4 promises made by God.

Exodus 6:6-8: So say to the Israelites, “I am Yahweh

I shall free you from the forced labor of the Egyptians – Cup of Sanctification

Luke 22:17-18

I shall rescue you from their slavery—Cup of Forgiveness.

I shall redeem you with outstretched arm and mighty acts of judgment—Cup of Blessing/Redemption

Traditionally the 3rd cup immediately followed the supper.1 Corinthians 11:23-25 "For I received from the Lord what I also passed on to you: The Lord Jesus, on the night he was betrayed, took bread, and when he had given thanks, he broke it and said, 'This is my body, which is for you; do this in remembrance of me"

Remembrance possibly refers to the mattan - free will gifts. Start of the betrothal period.

I shall take you as my people and I shall be your God”—Cup of Acceptance

Between the 3rd and 4th cup it was forbidden to drink wine. In the verse below we read Jesus didn’t drink that 4th cup until His kingdom would arrives. The next verse we read that directly after singing the hymn they went to mt Olives. Usually the 4th cup is taken directly after singing the hymn.

Matt 26:29-30 But I say to you, I will not drink from now on of this fruit of the vine, until that day when I drink it new with you in my Father's kingdom. And when they had sung an hymn, they went out into the mount of Olives.

Prov 31:6 When one is led out to execution, he is given a goblet of wine containing a grain of frankincense, in order to benumb his senses, for it is written,

The noble women in Jerusalem used to donate and bring it.” (Babylonian Talmud, Sanhedrin 43a).

John 19:23-30 Jesus, knowing that all was now finished, said “I thirst.” A bowl full of sour wine stood there; so they put a sponge full of the wine on hyssop and held it to his mouth. When Jesus had received the wine, he said, “It is finished”; and he bowed his head and gave up his spirit.

1. By vowing not to drink the final cup of the Last Supper, Jesus extended his last Passover meal to include his own suffering and death.

2. By praying three times in Gethsemane for the “cup” to be taken from him, Jesus revealed that he understood his own death in terms of the Passover sacrifice.

3. Jesus also transformed the Passover sacrifice. In the old Passover, the sacrifice of the lamb would come first, and then the eating of its flesh. But in this case, because Jesus had to institute the new

Passover before his death, he pre-enacted it, as both host of the meal and sacrifice.

4. Most important of all, by waiting to drink the fourth cup of the Passover until the very moment of his death, Jesus united the Last Supper to his death on the cross. By refusing to drink of the fruit of the vine until he gave up his final breath, he joined the offering of himself under the form of bread and wine to the offering of himself on Calvary. Both actions said the same thing: “This is my body, given for you”

(Luke 22:19). In short, by means of the Last Supper, Jesus transformed the Cross into a Passover, and by means of the Cross, he transformed the Last Supper into a sacrifice.

At midnight after the 4th cup the host closes the feast with the words "It is finished"

John 19:30 When Jesus therefore had received the vinegar, he said, It is finished: and he bowed his head, and gave up the ghost.

That was Jesus 4th cup.

The host of the Passover meal closed the feast at midnight (hour of darkness?) with the words “It is finished.”

Does that imply His kingdom started right at moment on the cross?

Note: The Passover ritual changed so often that the exact ritual during Jesus time is uncertain. Perhaps the names of the 3rd and 4th cup were switched ot there were only 3 cups during Jesus the Last Supper.

Jesus said I won’t drink any more until kingdom. In the garden he called crucifixion ‘a cup’ on the cross he drank wine. Did or dint he drink that last cup?

During the supper Jesus pours/gives wine but never are we told he drank it. He likely did because of the betrothal pattern.

"it is no longer I that live but Christ who lives in me"

lives in our mansion

Dregs

Mat 26:39 Going a little farther, he fell with his face to the ground and prayed, "My Father, if it is possible, may this cup be taken from me. Yet not as I will, but as you will."

What does the above exactly mean?

The usual interpretation is that Jesus asked Father if there was another way besides going to the cross and if so He would prefer that way if Father agrees.

In my opinion He asked the opposite.

A (very) large cup of wine was passed along with everyone being in the room.

The custom was that everybody took a big swig; not just a sip.

At those times wine wasn't as perfectly filtered as it's now and the bottom of the cup often contained bitter dregs.

So there was no cheating allowed by taking a tiny sip to avoid the dregs.

Once the cup was empty, the one that drank the dregs filled the cup again and passed it to the next person.

It was more like I want a fresh cup if wine to 'originate' from Me. And the only way that could be if He drank the dregs. Obviously the dregs refer to His suffering.

Isa 51:17 Awake, awake! Rise up, Jerusalem, you who have drunk from the hand of the LORD the cup of his wrath, you who have drained to its dregs the goblet that makes people stagger

Psalm 75:8 In the hand of Jehovah there is a cup, and He hath mixed with wine, He hath filled with the mixture, and hath poured out therefrom; but the dregs thereof, all the wicked of the earth shall suck them out, and drink them